74360-82-0

Basic information

• Product Name: tert-butyl N²-[(benzyloxy)carbonyl]-N¹-methyl-L-glutaminate
• Synonyms: tert-butyl N²-[(benzyloxy)carbonyl]-N¹-methyl-L-glutaminate
• CAS NO: 74360-82-0
• Molecular Weight: 350.415
• Mol File: 74360-82-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl N²-[(benzyloxy)carbonyl]-N¹-methyl-L-glutaminate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl N²-[(benzyloxy)carbonyl]-N¹-methyl-L-glutaminate(74360-82-0)
• EPA Substance Registry System: tert-butyl N²-[(benzyloxy)carbonyl]-N¹-methyl-L-glutaminate(74360-82-0)

Safety Data

• Hazardous Substances Data: 74360-82-0(Hazardous Substances Data)

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 74-89-5 methylamine 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 

Downstream Products

• 95064-33-8 (S)-4-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-methylcarbamoyl-butyric acid tert-butyl ester 
• 95064-39-4 (S)-4-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-methylcarbamoyl-butyric acid 
• 95063-94-8 (S)-4-Methylcarbamoyl-4-{4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-butyric acid tert-butyl ester 
• 95064-10-1 (S)-4-(4-Methylamino-benzoylamino)-4-methylcarbamoyl-butyric acid tert-butyl ester 
• 861820-02-2 N⁵-benzyloxy-N¹-methyl-N²-(4-methylbenzoyl)-L-glutamamide 
• 223466-98-6 tert-butyl N¹-methyl-N²-(4-methylbenzoyl)-L-glutaminate 
• 223466-99-7 4(S)-Methylaminocarbonyl-4-(N-(4-methylphenylcarbonyl)amino)butyric acid 

Relevant articles and documents

Novel matrix metalloproteinase inhibitors: Generation of lead compounds by the in silico fragment-based approach

Generation of structurally new matrix metalloproteinase inhibitors was successfully carried out using an in silico technique. In order to identify the small fragment interacting with residues in the S1′ pocket of MMP-1 through hydrogen bonds, we performed in silico screening using the LUDI program. As a result, acetyl-l-alanyl-(N-methyl)amide (Ac-l-Ala-NHMe) was selected to link with another fragment, hydroxamic acid that interacted with catalytic zinc. By this approach, the l-glutamic acid derivative 2b was discovered to be a new type of matrix metalloproteinase inhibitor. Further transformation to reduce its peptidic nature and improve activity yielded nonpeptidic lead compounds as inhibitors of MMP-1, -2, -3, and -9.

Synthesis of Monoamides of Methotrexate from L-Glutamic Acid Monoamide t-Butyl Esters

Analoques of methotrexate (amethopterin) (1) with α- or γ-monoamide functions were synthesized starting with t-butyl L-isoglutamine (12a), t-butyl L-glutamine (22a), or the appropriate N'-alkyl or N'N'-dialkyl analoques (12b-k), (22d), (22k), (22l), and (22m).The corresponding N-benzyloxycarbonyl compounds (11) and/or (21) from which the above L-glutamic acid derivatives were obtained were generally synthesized by mixed-anhydride coupling of N-benzyloxycarbonyl-L-glutamic acid (9) with the appropriate amine, conversion into the t-butyl ester, and chromatographic separation.The resulting α-monoamide γ-t-butyl ester (11) and γ-monoamide α-t-butyl ester (21) are unambiguously distinguished by mass spectrometry and 13C n.m.r. spectroscopy.Factors which affect the γ-amide/α-amide product ratio are discussed.The N-deprotected L-glutamic acid monoamide t-butyl esters (12) or (22) were individually coupled to N-trifluoroacetyl-p-methylaminobenzoic acid, and the resulting α- or γ-monoamide t-butyl esters (13) or (23) of N-(p-methyl(trifluoroacetyl)aminobenzoyl)-L-glutamic acid was hydrolysed.The N-deprotected product, viz. t-butyl N-(p-methylaminobenzoyl)-L-glutamate α- or γ-monoamide (14) or (24) was converted into the appropriate methotrexate-monoamide t-butyl ester (15) or (25), and thence the desired methotrexate-monoamide (16) or (26), by reaction with 2,4-diamino-6-bromomethylpteridine (17) or by the Taylor procedure.Features of the mass and 13C n.m.r. spectra of the intermediates are discussed.